Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships
Microbial transformation was used to prepare novel cytotoxic bufadienolides. Twelve products ( 3– 14) were obtained from bufalin ( 1) by the fungus Mucor spinosus. Their structures were elucidated by high-resolution mass spectroscopy (HR-MS) and extensive NMR techniques, including 1 H NMR, 13 C NMR,...
Gespeichert in:
| Veröffentlicht in: | The Journal of steroid biochemistry and molecular biology 2004-06, Vol.91 (1), p.87-98 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 98 |
|---|---|
| container_issue | 1 |
| container_start_page | 87 |
| container_title | The Journal of steroid biochemistry and molecular biology |
| container_volume | 91 |
| creator | Ye, Min Qu, Guiqin Guo, Hongzhu Guo, Dean |
| description | Microbial transformation was used to prepare novel cytotoxic bufadienolides. Twelve products (
3–
14) were obtained from bufalin (
1) by the fungus
Mucor spinosus. Their structures were elucidated by high-resolution mass spectroscopy (HR-MS) and extensive NMR techniques, including
1
H
NMR,
13
C
NMR, DEPT,
1
H
–
1
H
correlation spectroscopy (COSY), two dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond coherence (HMBC). Compounds
3,
4,
9 and
11–
14 are new mono- or dihydroxylated derivatives of bufalin with novel oxyfunctionalities at C-1β, C-7β, C-11β, C-12β and C-16α positions. The in vitro cytotoxic activities against human cancer cell lines of
3–
14, together with 16 biotransformed products derived from cinobufagin (
15–
30) were determined by the MTT method, and their structure–activity relationships (SAR) were discussed. |
| doi_str_mv | 10.1016/j.jsbmb.2004.01.010 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_66721477</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960076004002146</els_id><sourcerecordid>66721477</sourcerecordid><originalsourceid>FETCH-LOGICAL-c385t-d485f26cab3e810308a6f1c160314abb2f6a69b55bbd4dfeab2e3ed18a4521253</originalsourceid><addsrcrecordid>eNp9kc-KFDEQhxtR3NnVJxAkF73NWJV0p3sOHmTRVVj0oueQP9VMhu7OmKSHbbz4Dr6hT2J2Z0BPQkEO9dWPqi9V9QJhg4DyzX6zT2Y0Gw5QbwBLwaNqhV27XSPn8LhawVbCGloJF9VlSnsAEALbp9UFNlyiQFxVPz6HIw3MLjnkcOctM3OvnacpDN5RYo6iP5JjfQzjQ2_wEzMLG72NwXg9sN3iYrhbBp19mJieHMs78pGlHGeb50i_f_7SNvujzwuLdOLSzh_Ss-pJyUv0_PxeVd8-vP96_XF9--Xm0_W727UVXZPXru6ankurjaAOQUCnZY8WJQistTG8l1puTdMY42rXkzacBDnsdN1w5I24ql6fcg8xfJ8pZTX6ZGkY9ERhTkrKlmPdtgUUJ7DcllKkXh2iH3VcFIK6d6726sG5uneuAEtBmXp5jp_NSO7vzFlyAV6dAZ2sHvqoJ-vTP9y2q2sUhXt74qjIOHqKKtnyE5acj2SzcsH_d5E_8aalfQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>66721477</pqid></control><display><type>article</type><title>Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Ye, Min ; Qu, Guiqin ; Guo, Hongzhu ; Guo, Dean</creator><creatorcontrib>Ye, Min ; Qu, Guiqin ; Guo, Hongzhu ; Guo, Dean</creatorcontrib><description>Microbial transformation was used to prepare novel cytotoxic bufadienolides. Twelve products (
3–
14) were obtained from bufalin (
1) by the fungus
Mucor spinosus. Their structures were elucidated by high-resolution mass spectroscopy (HR-MS) and extensive NMR techniques, including
1
H
NMR,
13
C
NMR, DEPT,
1
H
–
1
H
correlation spectroscopy (COSY), two dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond coherence (HMBC). Compounds
3,
4,
9 and
11–
14 are new mono- or dihydroxylated derivatives of bufalin with novel oxyfunctionalities at C-1β, C-7β, C-11β, C-12β and C-16α positions. The in vitro cytotoxic activities against human cancer cell lines of
3–
14, together with 16 biotransformed products derived from cinobufagin (
15–
30) were determined by the MTT method, and their structure–activity relationships (SAR) were discussed.</description><identifier>ISSN: 0960-0760</identifier><identifier>EISSN: 1879-1220</identifier><identifier>DOI: 10.1016/j.jsbmb.2004.01.010</identifier><identifier>PMID: 15261311</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Bacteria - metabolism ; Biological and medical sciences ; Biological Assay ; Bufadienolide ; Bufalin ; Bufanolides - chemistry ; Cell Line, Tumor ; Chromatography, High Pressure Liquid ; Coloring Agents - pharmacology ; Cytotoxicity ; Enzyme Inhibitors - pharmacology ; Fundamental and applied biological sciences. Psychology ; Fungi - metabolism ; HeLa Cells ; HL-60 Cells ; Humans ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Microbial transformation ; Models, Chemical ; Mucor spinosus ; Oxygen - chemistry ; Spectrophotometry ; Structure-Activity Relationship ; Tetrazolium Salts - pharmacology ; Thiazoles - pharmacology ; Ultraviolet Rays ; Vertebrates: endocrinology</subject><ispartof>The Journal of steroid biochemistry and molecular biology, 2004-06, Vol.91 (1), p.87-98</ispartof><rights>2004 Elsevier Ltd</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-d485f26cab3e810308a6f1c160314abb2f6a69b55bbd4dfeab2e3ed18a4521253</citedby><cites>FETCH-LOGICAL-c385t-d485f26cab3e810308a6f1c160314abb2f6a69b55bbd4dfeab2e3ed18a4521253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960076004002146$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15984413$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15261311$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ye, Min</creatorcontrib><creatorcontrib>Qu, Guiqin</creatorcontrib><creatorcontrib>Guo, Hongzhu</creatorcontrib><creatorcontrib>Guo, Dean</creatorcontrib><title>Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships</title><title>The Journal of steroid biochemistry and molecular biology</title><addtitle>J Steroid Biochem Mol Biol</addtitle><description>Microbial transformation was used to prepare novel cytotoxic bufadienolides. Twelve products (
3–
14) were obtained from bufalin (
1) by the fungus
Mucor spinosus. Their structures were elucidated by high-resolution mass spectroscopy (HR-MS) and extensive NMR techniques, including
1
H
NMR,
13
C
NMR, DEPT,
1
H
–
1
H
correlation spectroscopy (COSY), two dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond coherence (HMBC). Compounds
3,
4,
9 and
11–
14 are new mono- or dihydroxylated derivatives of bufalin with novel oxyfunctionalities at C-1β, C-7β, C-11β, C-12β and C-16α positions. The in vitro cytotoxic activities against human cancer cell lines of
3–
14, together with 16 biotransformed products derived from cinobufagin (
15–
30) were determined by the MTT method, and their structure–activity relationships (SAR) were discussed.</description><subject>Bacteria - metabolism</subject><subject>Biological and medical sciences</subject><subject>Biological Assay</subject><subject>Bufadienolide</subject><subject>Bufalin</subject><subject>Bufanolides - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Coloring Agents - pharmacology</subject><subject>Cytotoxicity</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungi - metabolism</subject><subject>HeLa Cells</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Microbial transformation</subject><subject>Models, Chemical</subject><subject>Mucor spinosus</subject><subject>Oxygen - chemistry</subject><subject>Spectrophotometry</subject><subject>Structure-Activity Relationship</subject><subject>Tetrazolium Salts - pharmacology</subject><subject>Thiazoles - pharmacology</subject><subject>Ultraviolet Rays</subject><subject>Vertebrates: endocrinology</subject><issn>0960-0760</issn><issn>1879-1220</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc-KFDEQhxtR3NnVJxAkF73NWJV0p3sOHmTRVVj0oueQP9VMhu7OmKSHbbz4Dr6hT2J2Z0BPQkEO9dWPqi9V9QJhg4DyzX6zT2Y0Gw5QbwBLwaNqhV27XSPn8LhawVbCGloJF9VlSnsAEALbp9UFNlyiQFxVPz6HIw3MLjnkcOctM3OvnacpDN5RYo6iP5JjfQzjQ2_wEzMLG72NwXg9sN3iYrhbBp19mJieHMs78pGlHGeb50i_f_7SNvujzwuLdOLSzh_Ss-pJyUv0_PxeVd8-vP96_XF9--Xm0_W727UVXZPXru6ankurjaAOQUCnZY8WJQistTG8l1puTdMY42rXkzacBDnsdN1w5I24ql6fcg8xfJ8pZTX6ZGkY9ERhTkrKlmPdtgUUJ7DcllKkXh2iH3VcFIK6d6726sG5uneuAEtBmXp5jp_NSO7vzFlyAV6dAZ2sHvqoJ-vTP9y2q2sUhXt74qjIOHqKKtnyE5acj2SzcsH_d5E_8aalfQ</recordid><startdate>20040601</startdate><enddate>20040601</enddate><creator>Ye, Min</creator><creator>Qu, Guiqin</creator><creator>Guo, Hongzhu</creator><creator>Guo, Dean</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040601</creationdate><title>Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships</title><author>Ye, Min ; Qu, Guiqin ; Guo, Hongzhu ; Guo, Dean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-d485f26cab3e810308a6f1c160314abb2f6a69b55bbd4dfeab2e3ed18a4521253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Bacteria - metabolism</topic><topic>Biological and medical sciences</topic><topic>Biological Assay</topic><topic>Bufadienolide</topic><topic>Bufalin</topic><topic>Bufanolides - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Coloring Agents - pharmacology</topic><topic>Cytotoxicity</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungi - metabolism</topic><topic>HeLa Cells</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Microbial transformation</topic><topic>Models, Chemical</topic><topic>Mucor spinosus</topic><topic>Oxygen - chemistry</topic><topic>Spectrophotometry</topic><topic>Structure-Activity Relationship</topic><topic>Tetrazolium Salts - pharmacology</topic><topic>Thiazoles - pharmacology</topic><topic>Ultraviolet Rays</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ye, Min</creatorcontrib><creatorcontrib>Qu, Guiqin</creatorcontrib><creatorcontrib>Guo, Hongzhu</creatorcontrib><creatorcontrib>Guo, Dean</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>The Journal of steroid biochemistry and molecular biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ye, Min</au><au>Qu, Guiqin</au><au>Guo, Hongzhu</au><au>Guo, Dean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships</atitle><jtitle>The Journal of steroid biochemistry and molecular biology</jtitle><addtitle>J Steroid Biochem Mol Biol</addtitle><date>2004-06-01</date><risdate>2004</risdate><volume>91</volume><issue>1</issue><spage>87</spage><epage>98</epage><pages>87-98</pages><issn>0960-0760</issn><eissn>1879-1220</eissn><abstract>Microbial transformation was used to prepare novel cytotoxic bufadienolides. Twelve products (
3–
14) were obtained from bufalin (
1) by the fungus
Mucor spinosus. Their structures were elucidated by high-resolution mass spectroscopy (HR-MS) and extensive NMR techniques, including
1
H
NMR,
13
C
NMR, DEPT,
1
H
–
1
H
correlation spectroscopy (COSY), two dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond coherence (HMBC). Compounds
3,
4,
9 and
11–
14 are new mono- or dihydroxylated derivatives of bufalin with novel oxyfunctionalities at C-1β, C-7β, C-11β, C-12β and C-16α positions. The in vitro cytotoxic activities against human cancer cell lines of
3–
14, together with 16 biotransformed products derived from cinobufagin (
15–
30) were determined by the MTT method, and their structure–activity relationships (SAR) were discussed.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15261311</pmid><doi>10.1016/j.jsbmb.2004.01.010</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-0760 |
| ispartof | The Journal of steroid biochemistry and molecular biology, 2004-06, Vol.91 (1), p.87-98 |
| issn | 0960-0760 1879-1220 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_66721477 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Bacteria - metabolism Biological and medical sciences Biological Assay Bufadienolide Bufalin Bufanolides - chemistry Cell Line, Tumor Chromatography, High Pressure Liquid Coloring Agents - pharmacology Cytotoxicity Enzyme Inhibitors - pharmacology Fundamental and applied biological sciences. Psychology Fungi - metabolism HeLa Cells HL-60 Cells Humans Magnetic Resonance Spectroscopy Mass Spectrometry Microbial transformation Models, Chemical Mucor spinosus Oxygen - chemistry Spectrophotometry Structure-Activity Relationship Tetrazolium Salts - pharmacology Thiazoles - pharmacology Ultraviolet Rays Vertebrates: endocrinology |
| title | Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure–activity relationships |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T23%3A03%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Novel%20cytotoxic%20bufadienolides%20derived%20from%20bufalin%20by%20microbial%20hydroxylation%20and%20their%20structure%E2%80%93activity%20relationships&rft.jtitle=The%20Journal%20of%20steroid%20biochemistry%20and%20molecular%20biology&rft.au=Ye,%20Min&rft.date=2004-06-01&rft.volume=91&rft.issue=1&rft.spage=87&rft.epage=98&rft.pages=87-98&rft.issn=0960-0760&rft.eissn=1879-1220&rft_id=info:doi/10.1016/j.jsbmb.2004.01.010&rft_dat=%3Cproquest_cross%3E66721477%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=66721477&rft_id=info:pmid/15261311&rft_els_id=S0960076004002146&rfr_iscdi=true |